p-Toluenesulfonic acid → HCID 22407599, compound

HRID 1756007Notes

Reaction equation

HRID 1756007 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.O1CCCCC1[O:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][NH:29][C:30]2[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:34]([CH2:41][CH3:42])[N:33]=[CH:32][N:31]=2)=[CH:23][CH:22]=1>C(O)C>[OH:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][NH:29][C:30]2[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:34]([CH2:41][CH3:42])[N:33]=[CH:32][N:31]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22407596HCID 22407596, compound

Product 1

HCID 22407599HCID 22407599, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-Toluenesulfonic acid (0.10 g) was added to a solution of ethyl 4-(2-(4-(2-(tetrahydropyran-2-yloxy)ethyl)phenyl)ethylamino)-6-ethylpyrimidine-5-carboxylate (4.20 g, 9.82 mmol) in ethanol (40 ml). The mixture was heated under reflux for 4 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. Water (40 ml) was added to the residue. The mixture was extracted with methylene chloride and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=1/1) to give the desired ethyl 4-(2-(4-(2-hydroxyethyl)phenyl)ethylamino)-6-ethylpyrimidine-5-carboxylate (2.60 g, 77%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customthe solvent was evaporated under reduced pressure
  4. additionWater (40 ml) was added to the residue
  5. extractionThe mixture was extracted with methylene chloride
  6. dry with materialdried over magnesium sulfate
  7. customAfter evaporation of the solvent
  8. customthe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=1/1)

Sources & evidence

ORD record
ord-2e4f93c111f54e989323caeb0d89ff20
Source dataset
uspto-grants-1995_08
Patent number
US05439911

Reaction notes

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